(4S,5S)-5-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-but-2-ynyl]-4-[4-(4-methoxy-benzyloxy)-but-1-ynyl]-oxazolidin-2-one

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Chemical Name:(4S,5S)-5-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-but-2-ynyl]-4-[4-(4-methoxy-benzyloxy)-but-1-ynyl]-oxazolidin-2-one
CAS No.:780769-14-4
Molecular Formula:C₂₅H₃₅NO₅Si
Molecular Weight:457.642
Hs Code.:

Synonyms:(4S,5S)-5-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-but-2-ynyl]-4-[4-(4-methoxy-benzyloxy)-but-1-ynyl]-oxazolidin-2-one

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Chemical Property of (4S,5S)-5-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-but-2-ynyl]-4-[4-(4-methoxy-benzyloxy)-but-1-ynyl]-oxazolidin-2-one

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Technology Process of (4S,5S)-5-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-but-2-ynyl]-4-[4-(4-methoxy-benzyloxy)-but-1-ynyl]-oxazolidin-2-one

There total 5 articles about (4S,5S)-5-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-but-2-ynyl]-4-[4-(4-methoxy-benzyloxy)-but-1-ynyl]-oxazolidin-2-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 75.0%

: (4S,5S)-5-(1-Hydroxy-but-2-ynyl)-4-[4-(4-methoxy-benzyloxy)-but-1-ynyl]-oxazolidin-2-one

: 18162-48-6
tert-butyldimethylsilyl chloride

: (4S,5S)-5-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-but-2-ynyl]-4-[4-(4-methoxy-benzyloxy)-but-1-ynyl]-oxazolidin-2-one

: 780769-14-4
(4S,5S)-5-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-but-2-ynyl]-4-[4-(4-methoxy-benzyloxy)-but-1-ynyl]-oxazolidin-2-one

Guidance literature:: With 1H-imidazole; In dichloromethane; at 20 ℃; for 6h;
DOI:10.1002/anie.200460058

Reference yield:

: 780769-10-0
(4S,5S)-5-Hydroxymethyl-4-[4-(4-methoxy-benzyloxy)-but-1-ynyl]-oxazolidin-2-one

: 780769-14-4
(4S,5S)-5-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-but-2-ynyl]-4-[4-(4-methoxy-benzyloxy)-but-1-ynyl]-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 °C / Moffatt-Swern oxidation

1.2: 50 percent / zinc chloride / tetrahydrofuran / -78 - 2 °C

2.1: 75 percent / imidazole / CH₂Cl₂ / 6 h / 20 °C

With 1H-imidazole; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane;
DOI:10.1002/anie.200460058

Reference yield:

: Allyl-[1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-(4-methoxy-benzyloxy)-pent-2-ynyl]-amine

: 780769-14-4
(4S,5S)-5-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-but-2-ynyl]-4-[4-(4-methoxy-benzyloxy)-but-1-ynyl]-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: Pd(dba)2; 1,4-bis(diphenylphosphanyl)butane; 2-thiosalicylic acid / tetrahydrofuran / 0.67 h / 60 °C

1.2: 99 percent / aq. sodium bicarbonate / tetrahydrofuran / 0.5 h / 20 °C

2.1: p-toluenesulfonic acid monohydrate / methanol / 12 h

2.2: 88 percent / aq. potassium carbonate / methanol / 20 °C

3.1: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 °C / Moffatt-Swern oxidation

3.2: 50 percent / zinc chloride / tetrahydrofuran / -78 - 2 °C

4.1: 75 percent / imidazole / CH₂Cl₂ / 6 h / 20 °C

With 1H-imidazole; oxalyl dichloride; toluene-4-sulfonic acid; dimethyl sulfoxide; Thiosalicylic acid; triethylamine; 1,4-di(diphenylphosphino)-butane; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1002/anie.200460058